These Over 50 Dating Tips May Shock (or Even Annoy) You… But, they Work

Forget the aging stereotypes! Women over 50 are vibrant, emotional and sexual beings. Many of us are interested in over 50 dating, even if we don’t have any intention of getting married again. We just need a little advice on how to get started.

My guest on today’s episode of the Sixty and Me Show is dating coach, Lisa Copeland. Join us as we discuss how to find love – or at least a little romance – in your 50s, 60s or better! Enjoy the show!

Margaret Manning:

Hello everyone! This is Margaret Manning with Sixty and Me. This is the place where women over 60 come to be inspired.

One of the things we care about in the community is our independence. This could be related to finding love again, after a life of disappointments or divorce. It could also be finding ourselves on our own after 60.

My guest today, Lisa Copeland, is a dating coach. She specializes in women over 50, and she writes for the Huffington Post. She’s also published several books. She has been through on online dating journey and several divorces and is perfectly qualified to discuss this subject. Lisa, welcome to this show.

Lisa Copeland:

Hi, Margaret! It’s so nice being here. Thank you for inviting me.

Margaret:

Tell us about your journey to becoming a dating coach.

Lisa:

I would love to. My first marriage lasted 24 years. My then husband, who is the father of my children, and I simply grew apart. For us, this ended up with a divorce. Afterward, I took about a year to heal. I firmly believe that healing after the end of a relationship is super important. A lot of people jump from one relationship to the next without giving themselves the time to really establish who they are.

I was in my 40’s then, surrounded with friends who didn’t know single people. Thus, I ended up going online. It was crazy because I did some of the dumbest things ever. I posted a picture online of my dad with me. Men would ask, “Is that your ex-husband?” I also wrote things in my profile that were not appropriate. I thought they were romantic but were not the right things to say.

Men weren’t asking me out on second dates and I didn’t understand why. I felt rejected. I was struggling, and it was very painful. I did end up in a relationship with a man I met online. It lasted for 2 and a half years. As he walked out the door, he said to me, “Lisa, you don’t know how to let a man be a man.”

I thought, “He’s crazy, I get along with men really well,” and I just blew off the comment. Then, after a pause I took to heal, I went back online. Eventually, I met my second husband. We had tremendous chemistry. However, it turned out to be so strong that it was only a physical chemistry. There wasn’t a friendship beneath it.

Within two years of marrying, we were divorcing. He, too, said to me, “Lisa, you don’t know how to let a man be a man.” That’s when I thought, “Oh my God, I’m doing something wrong.”

Margaret:

There’s a big message there.

Lisa:

I came out of that divorce, feeling like I really failed. I thought, “Who’s going to want me? I’ve been divorced twice.” If you really listen to people, you’ll learn that many of them have been divorced twice or more. That’s when I went looking for a coach.

Coaches, though, were pretty young. At that time, they were in their 20’s and 30’s. There are a couple now, in their 40’s. There are also male coaches close to 50, but I couldn’t tell my stuff to a man. You can’t talk about your body to a man. This is something you wouldn’t feel comfortable with. With the female coaches being my kid’s age, I thought, “I can’t talk to them about it.”

I started researching dating with a different perspective. I began with figuring out this business about, “Lisa, you don’t let a man be a man.” I found all the tools that were needed, and I put all my newly gained knowledge into practice. I figured out what worked and what didn’t. The result was that I started getting second dates. I started having a great time dating. I didn’t dread it anymore—it was fun. I did end up in a relationship.

The truth though is, over 50’s dating is very, very different from dating in your 20’s, in the way that relationships go.

Margaret:

What you just described is the journey that so many women over 50 take. Also, dating over 50 is one thing, but when you get to 60, it becomes a very different category. There is something that has been on my mind since I interviewed Suzanne Bron-Levine a few weeks ago. She is the first editor of Miss Magazine and has been women’s advocate throughout the last six decades.

A lot of women in our community were raised through those decades. Women’s lib and independence happened within that time frame, allowing us to do things for ourselves. Do you think that the way we were raised back then has impacted or impacts the dating opportunities for us?

Lisa:

We all grew up through the years of the women’s lib movement. This was fantastic for getting us into the workplace and for getting us to use our brains again. What also happened, though, was that our newly gained independence took us against our natural DNA patterns between men and women. We’ve been fighting those patterns ever since.

That is why two of the men I was with left saying, “You know Lisa, you don’t know how to make me feel like a man.” The reality is, I truly didn’t. We were taught “Walk over men. You could do it as well. You can do it better and you don’t need a man.”

Now we do want men in our lives, but we don’t know how to relate to them because we weren’t taught that. Instead, it was all about competition.

Margaret:

Please, go on. This reminded me of a sign I had on my desk when I was in the working world. It said, “A woman has to try twice as hard to be considered half as good as a man. Fortunately, that’s not too difficult.”

We used to laugh at the fact that we were getting ahead of men; that we were competing and succeeding. Please tell us a little bit more about how this competition in the work place imbalanced the relationship between the strong alpha male and the receiving woman.

Lisa:

What was happening was that competition between men and women increased to a point where women couldn’t get into a partnership with men to work or live together. We were never taught how to become partners. We thought we did everything so well that it was pretty much our way or the highway.

My main goal is getting women into partnerships with men in both work and home. Being a dating coach, it’s interesting that I do attract a lot of women in situations similar to my own. I’ve been through the same thing and overcome the problem. Now I can teach others how to do it, too.

I have a female client, who is a CEO. She had to meet a very high powered man for an important deal. However, in the past her relationship with him was painful because she could not get the deal sealed.

The problem was that she was fighting. She was competing with him, going in with facts and figures. One of her mistakes was going in the meeting in a man-style, black suit with heavy glasses. It’s not surprising that nothing got done.

The next time she had to meet the same man, she took the advice I taught her about dating and applied it. She went into her meeting, and she asked the man the four magic words, “Could you help me?” Within five minutes the deal was sealed. Ever since, he has done everything possible to help her.

We should really understand that we don’t have to step on men. We don’t have to dumb down, nor should we be doormats. We just have to come into the natural female role that we’ve forgotten how to do, which is getting into a partnership with a man and letting them help us. Does that make sense?

Margaret:

Yeah, it makes perfect sense. In the very beginning, one of our goals in this community is to become independent. I think this concept is largely misinterpreted. It doesn’t mean that we should accomplish it at the expense of receiving from people, rather than trying to do and give what we can.

Lisa:

One of the biggest problems we have developed because we were taught to give, to nurture. By over giving we became superwomen. However, over giving as a male quality. Women are supposed to be the receivers. This is a whole different way of thinking, actually. That’s why, when I write about this, a lot of women get very angry.

In actuality, we’ve all lost because of this. We’ve lost our femininity, which is our power. We became masculine females, and this is not a powerful place to be. It’s like pushing guys on the way up versus working together.

Margaret:

What you said about feminine power really is an interesting point. David Wygant, who’s also a dating coach, said exactly the same thing, giving the male perspective. He said we shouldn’t wait to say something, but make the man feel honored.

When I heard that, I thought, “Oh my God, why would I want to make a man feel honored? He’s supposed to be the warrior coming after me. Why should I be flirty and seductive?” What’s your point of view?

Lisa:

If you want to be involved with an alpha man, you should keep in mind several things. One of these is that you need to show him respect at every turn. In return, he will cherish you and do everything possible to make you happy.

Look at my client, the CEO. She respected the man’s opinion, and that made him turn around and do everything possible to make the deal work. Whereas in the past, when she competed with him, he would just compete back.

Men don’t want to compete with women in relationships. They do enough of that with other men. In relationships with women, men want to have an emotional connection.

Margaret:

This is a great topic. That shift in mindset that you’re describing is really important. You say that we have to let go of some of our control and, instead, place our feminine side on the front line. I’ve heard a lot of women say, “I may appear to be very strong and aggressive, but actually I do want to be looked after and nurtured.” Based on your advice, women must let their true selves come out to make that partnership connection.

Lisa:

Definitely. If you can find your true femininity, you should let it out. The key is refinding it and recognizing it is as much more powerful than the masculine female. Being masculine is not a powerful place for a female over the long haul because you can’t get the cooperation of men that way.

Margaret:

A lot of women over 50 and 60 will say that they don’t have any success with dating. You mentioned that you had similar experience in your own life. Could you tell us about some of the misconceptions that we might have about the dating game right now? What is preventing us from experiencing successful dating? What sides in our mindset do we have to change?

Lisa:

I think misconception number one is that women think they know how to date. However, most women did not date when they were younger, they simply fell into the relationships.

Margaret:

That’s true.

Lisa:

They’re missing the tools and the skills needed for over 50 dating. That’s what I teach women—the tools and skills—because it is a learned factor. Whether you’re in your 50’s or 60’s it’s the issues are very common.

The first mindset group of women go online and when they see men their age, they think of them as they would of their daddies and granddaddies. We all want to be dating George Clooney, who, by the way, doesn’t really like long term relationships. This is typical of the over-fifty age group, though.

Margaret:

So, one of our problems is that we look for George Clooney in all our relationships.

Lisa:

We also date like we’re still 20. Number one reason why we feel so bad about ourselves is that we compare ourselves to our 20-year-old self. We tend to do that because, for many of us it was the last time we were out on the market.

Embracing the awesomeness of who we are is part of what I teach women. This is the basic foundation, because if we don’t feel good about ourselves, we give our power away to men by worrying, “Do they like me?” versus “Do I like them?”

The other thing about online dating—which is where most women meet men—that we should keep in mind is its one dimensionality. Women do think that the men on there look like their daddies and granddaddies. In person though, they may not look this way.

For example, when you see somebody online you might think “No way!” When you see them in person though, you may go, “Hmm there’s a personality. I can see who he really is.” Basically, we don’t give enough men a chance.

Margaret:

We also expect this instinct chemistry with people. You look at a profile and you say, “There’s no chemistry,” and you immediately move on to the next one. We think that chemistry has to be instant. We want the George Clooneys, the beautiful people, to be in our lives only. Thus, we don’t know how to date.

When we were younger we just fell into situations with friends. For women over 50 though, meeting men online is safe.

Lisa:

Online dating sites are about the only place where people over 50 congregate. When we were younger, we met in school or college and maybe at work. Nowadays, young people go to clubs, but we don’t usually go to clubs and bars. We don’t feel as comfortable, so online remains the only safe place to women our age.

Margaret:

There is one question that always comes up, and I would just like your insight. Why do older men write on their profile “looking for younger women”? What’s going on there?

Lisa:

Many of the men I’ve spoken with have said, “Women look so old!” They have the same problem we do—in their mind we look like their mommies and grand mommies. This creates a rift in perception. Whereas people in their 30’s and 40’s look like the people who surrounded us when we were younger. I think that men look at those younger women and go, “Yes, this is who I remember.” But, they too, if they met a woman our age in the real world, would give her a chance.

Another thing, which is connected to our alpha female thinking, is that we forgot how to appreciate men. Younger women are more appreciative of an older man, but a lot of younger women don’t want the older men. Also, there are a lot of men our age who do want women our age. They want us within three to five years, because we share history together.

Margaret:

You’re right. A lot of younger women are more appreciative of an older man if he’s got money or power or something else that’s attractive. Once you get past that you can then bring out your real qualities. What tips can you give us concerning men that we should know but don’t? What have you learned in your experience? What do men want?

Lisa:

Beta men are different from alpha men. Here we cover alpha male behavior. Number one, they do want to be appreciated and thanked. We stopped doing that for our husbands when we were all married, and got used to it.

Secondly, they don’t want to be criticized. A man is willing to do anything for you. His goal, especially with older men, is to make you happy. When we criticize them, they won’t try to please us again. They’ll say, “I don’t need to do this for you,” and they will just move on.

The third thing about men is, they don’t want you to make them into your pet project—change their clothes, change their hair, etc. Either like a man for who he is, or don’t. Now there are some clothing things down the road you could possibly have an influence in. However, this is not the thing that you try to manipulate on a first date. You can’t say, “You know, I have a suggestion for you. Those shoes …”

I would say these are the three main things about men that women should be aware of. There’s plenty more, which I teach my clients. These though, are the top three things that can help women right away.

Margaret:

With all your tips we now know how to talk to a man. We know how to be place our femininity up front. What’s left is finding those men. Where do we go to look for them?

Lisa:

Over 50 dating online is the best.

Margaret:

Okay, let’s expand on this topic.

Lisa:

Online dating is the place where most men and women congregate when they go over 50. The second best way to find a man is by asking your dating fairy godmothers. These are your friends, your colleagues, any one that you know. “Do you know someone single?” You can’t ask them just once because it doesn’t stick in their head. You have to keep going back. A lot of married people really don’t know single people. They have one or two friends that are single, so they can’t be of much help.

In reality, you are the person who has to figure things out on how to meet men. Another way to do it is to look on Facebook at the people you went to high school with. You could also go to your high school or college reunion and see who’s single again.

Some women prefer to meet with men the ‘organic way.’ If you want to do that, the real key is getting yourself out there. The problem with this approach is that women who want to meet men face to face, don’t know how to flirt with them. This makes the ‘organic way’ equally as hard as the online dating method.

A good idea to overcome this difficulty is to think of activities that you love. You want to have the passion built back inside of you. We as women turn like pretzels to please the men we like, and we give ourselves up. The thing that men are so attracted to in women though, is their passion.

Get out there and find the things you really like doing. Play tennis, for instance, or go to a cooking class. You could run into someone that way. Think of places where men could be. These are all examples I’ve listed in that free report.

There are tons and tons of places, like a dog park. Get a dog and go to a dog park. There are all kinds of places. Men are really everywhere. Talk to them inline at Starbucks when you’re getting your coffee. No matter what age they are, get back and practice talking to men. That’s a big thing women aren’t doing. You can’t just suddenly start dating when you don’t even know how to talk to men.

Margaret:

I do that often. Men look at me with such astonishment sometimes. I’ll stand in line and say, “What’s good here? Have you ever tasted the chocolate muffins here?” It’s always just a really natural thing to do. The most important thing though, like you said, is to do the things we love.

Sports events are great because everybody is yelling and screaming and totally relaxed. There are always people passing food around, and, certainly, in the States this is very common.

Let’s move on to online over 50 dating. I’m a bit of a virgin with online dating myself, so I could do with some hints. Tell us the range of options that are out there, paid and unpaid, and just give us some advice and recommendations.

Lisa:

I am one of those dating coaches that believe unpaid sites are fine, too. There’s a lot of people that don’t believe in unpaid services, but I think, especially for our age group, they’re fine. A lot of men have profiles on both the paid and unpaid sites.

The nice thing about the unpaid is that everybody can write to everybody. On the paid sites, you have to be a paid member to write. A lot of women feel really rejected when men don’t write them back. By the way, writing to a man is not the best thing to do.

Most men will write you back to be nice, but it usually fizzles because the attraction has to start on his side. A guy has to be interested in you first. A fascinating thing to consider is that we may not be that interested in a guy, but once we get to know them, men grow on us. Then, because we get to know their personality, we start thinking that the guy who wasn’t so cute, is really cute.

Margaret:

You said not to make the first communication. What about features like winking and flirting?

Lisa:

Flirting is fine. You shouldn’t e-mail them unless it’s extremely flirty like, “I think you’re really cute. What are you doing on here?” You can say, “I’m interested in you,” or “I like your profile.” They’ll respond, but it usually fizzles.

Men have to do. They have to go by their attraction factor first. That’s important because they are very visual. This is why men are dating younger women. They certainly don’t get it, but if they meet these younger women in real life, they usually lose interest. They just don’t share the same history.

The other thing about online dating is your profile. Men usually write books and tell you what they don’t want and what they do want, while women write the most boring profiles like, “I love knitting. I love being in my garden. I love cutting flowers.” Getting rid of all those ‘I’s’ is where you should get started.

I like to think of online dating as a virtual cocktail party. When you’re at a cocktail party, you don’t tell a man, “I love gardening. I love pink flowers.” Your profile needs to be like a little story. I teach women how to do this, too. Make it into a story that intrigues a man to want to get to know you.

Your picture is also really important. I’ve had clients over 60 who had never gotten a hit with the pictures they’d posted. When we work together, I tell women it’s okay to get a professional photograph if it’s natural looking. You shouldn’t get it super retouched though because you want to look like yourself. Still, you want pictures of you that are flattering.

Show a man who you really are, and either they will like you or they won’t like you. You really don’t want men that don’t like you in your life. You want the men that like you. Yet, we so often try to turn those men that don’t like us into men that will like us and that’s not going to get anywhere.

Margaret:

Do you lie about your age?

Lisa:

Never. The biggest complaints both men and women have are, one, people don’t look like their pictures, and two, the people lied about their age. If you want to start a relationship, you’d likely want it to be with someone who wants to be with you at the age you’re at. You don’t want to start off with a lie, because then they’ll go, “Oh my God! You lied about this—what else are you gonna lie about?”

I think it’s better to be honest. Show yourself for who you are, take a full body shot. If you’re heavy, they’re not going to like you any better when they meet you. It’s a lot like false advertising, and men get really angry at that. And women do, too.

When a guy shows up and he’s 600 pounds, you’re not going to be happy. It goes back to wanting the people that want us. Stop trying to go for the people that don’t want us.

Margaret:

You’ve got wonderful ideas and offer coaching opportunities, and I want to make sure everybody knows where to go to find you. I’m going to put your website address up again. I know you do individual coaching and remote coaching over telephone or Skype.

Lisa:

I also do group coaching. There’s a benefit to the group one as well as one on one.

Margaret:

That’s great! I know the first call with you is complimentary. I really think that’s a great idea, just to have a few minutes to chat with you. You are infectious. I love your energy.

There are a couple more things I’d like to ask you really quickly. Who should make the first move? Some people in the community say that they don’t think it’s their job to make the first move. They wait for a man to reach out to them, either call them or notice them somewhere. I know a lot of people feel the opposite way, that women should feel free to make the first move. What’s your opinion about that?

Lisa:

You cannot write the first email, which doesn’t mean you can’t lead a man to asking you to go out. Men are very, very fearful of rejection. They’re the ones getting rejected the most. We get rejected, too, but on a much smaller scale. The way to gently let a man go could be playful, like, “Hey, if you ever feel like going to coffee, here’s my number.” By doing that, you’re offering a suggestion. You’re letting him come back and do the asking.

He has to be the one asking. If you say, “Hey you wanna go out for coffee?” he’s probably going to say, “Yeah, sure” That doesn’t mean he’s attracted to you though. Also, it doesn’t mean he doesn’t think of you as a friend. In fact, if he was attracted to you, he would probably ask you out, though not necessarily because men are afraid to.

I teach women how to give men signals, so that men would want to ask them out. I still content that it is much harder for us to do in the real world. It’s a little bit easier to do online with the winks and those kinds of things.

Margaret:

You have given us so much advise and so many tips. I’m really excited! I would actually like to have you back on again and go through this in a little bit more detail. For now, I just want to make sure we highlighted the fact that you have just released or are about to release a new book. It’s called “The Winning Dating Formula for Women Over Fifty.” Tell us about it. When is it coming out? how can we get it? What’s it about?

Lisa:

There are so many dating coaches out there talking about dating in your 20’s, 30’s and 40’s. That is a very different time in our lives. In our 50’s, we are usually not real clear on what we want in relationships. Because of that, we’re dating like we are in our 20’s, looking for George Clooney to have babies with. Dating when you’re over 50 is definitely a different way to date.

That’s why I wrote a book. I wanted women to understand that they need specific tools and skills to date at this age. The book came out the week of October 8th. If you sign up for my free report, you’ll get my blog posts in your e-mail inbox along with a letter. In that letter you will find out how to get the book for free for four days in October on Amazon.

The best thing to do is to sign up for that free report and then start watching next week for the blog and other emails.

Margaret:

When can we get the book for free?

Lisa:

10th and 11th of October and then 30th and 31st.

Margaret:

There are four dates then. Perfect!

Lisa:

If you would like a hard copy book, that will be out there also. That one won’t be free, but you can buy a hard copy book and Amazon will send it to you.

Margaret:

So this is a free Kindle download?

Lisa:

Yes, and anybody can download Kindle reading software to any technological apparatus they have, for free.

Margaret:

That is great! Thank you so much for writing that book. I can’t wait to read it and use all the tips that I know it has. I’m just so thrilled you have taken the time to talk to us today, Lisa. Thank you, again. I appreciate it very much.

Lisa:

It’s all my pleasure, Margaret. I had so much fun and I would love to come back any time. We can talk about something a bit deeper that maybe your audience wants to know more about.

Margaret:

I would want you to just take two minutes and tell us anything that you think is good advice for us. Last minute shout out to those 33,000 women over 60. What would you say to them?

Lisa:

Don’t think that you have to figure out if a guy is your next husband in the first 15 minutes of meeting him. Get out there and do what I call date to date. Have fun with men. You can end up dating, or whether you’re 50, 60 or 70 you can also have men as friends.

While you’re looking for the right guy, you can still find male companionship. Most women feel like they have to be marrying a guy or he’s not right. Actually, there is a grey area in-between and that’s friendship. Have fun and be around male energy. That’s really, really important for getting your game on for dating.

Margaret:

Fantastic! Thank you again for being here. I look forward to reading your book and having you back in the future.

Lisa:

Thanks, Margaret.

Have you tried over 50 dating? What advice would you like to offer to the other women in our community? Do you have any questions for Lisa? Please join the conversation.

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Margaret Manning is the founder of Sixty and Me. She is an entrepreneur, author and speaker. Margaret is passionate about building dynamic and engaged communities that improve lives and change perceptions. Margaret can be contacted at margaret@sixtyandme.com

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